Hillsborough Oaks

Hillsborough Oaks neighborhood is all about subtlety and grace

Hillsborough Oaks doesn’t announce itself with blaring horns and balloons. Instead, it simply evolves, appearing on quiet residential lanes as they head west out of Burlingame. Suddenly, the atmosphere quiets. Thick foliage replaces neatly-trimmed trees and the homes get larger. Hillsborough Oaks, a smaller (population approximately 800, total area of a half-mile square) neighborhood in lower Hillsborough bordering the southern edge of Burlingame’s Easton Addition, is about subtlety and grace. Like Ryan Tract, its next-door neighbor, Hillsborough Oaksbridge has been impressive for so long that there’s no one left to impress.

Also unique is Hillsborough Oaks location, within walking distance of Burlingame’s Broadway downtown neighborhood. Easy access to shopping and dining, El Camino Real and the 101 freeway makes this a neighborhood for pragmatists, something singer/actor Bing Crosby must have considered when he purchased a home on Jackling Drive in the 1960s. Crosby lived in the home until his passing. His widow Kathryn Crosby, continues to live there today. The home was one of five homes featured on the 2010 Hillsborough Centennial Historic Homes Tour.

At first glance things seem quieter for Hillsborough Oaks. After a 2021 in which its overall sales rose 83% and average home values 32%, Hillsborough Oaks reversed course in 2022, losing $1 million of average value (from $7.65 million in 2021 to $6.53 million in 2022) and 36% of overall sales (from 11 to 7). Look more closely, though, and the story brightens. Hillsborough Oaks saw a 24% gain in price per square foot in 2022, to $1,718. It also more than halved its average DOM, from 96 in 2021 to 43 last year. And while 2021’s property values were driven by a top-heavy market (three homes sold for $10 million-plus), 2022’s sales were grouped between $4.1 and $9.5 million, with 71% of all sales (falling between $5 and $8 million).

To view a detailed google map of the Hillsborough Oaks neighborhood, click here.

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Pricing data based on single-family homes

Hillsborough Oaks on the Map

Hillsborough Real Estate Market Review

In my 12th annual review of the Hillsborough residential real estate market, I examine 2023 market trends and relevant sales statistics. You'll learn first-hand what’s happening in your neighborhood.

Schools & History


The elementary school for Hillsborough Oaksbridge is North Hillsborough Elementary, located in the Country Manor neighborhood on Eucalyptus Avenue. It’s about a 4-6 minute drive from Hillsborough Oaksbridge.

There is one public middle school in Hillsborough, Crocker Middle School, which is located in the Country Club Manor neighborhood on Ralston Avenue. It’s a 6 minute drive from Hillsborough Oaksbridge and located next to North Hillsborough Elementary School.

Hillsborough does not have its own public high school. Most of the residents in the neighborhood attend Burlingame High School, located in Burlingame on Mangini Way. To search a high school by a specific address using a School Locator, click here.

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